Place the hulled strawberry and simple syrup in a cocktail shaker. Gently muddle to release the strawberry juices.
Add bourbon, fresh lemon juice, and Angostura bitters to the shaker. Fill with ice and shake vigorously for about 15 seconds until well chilled.
Strain the mixture into a highball glass filled with fresh ice. Top with ginger beer and gently stir. Garnish with a strawberry slice and a lemon wheel.